Acylated aminophenylsulfonylureas, processes for their preparation and their use as herbicides and plant growth regulators.
The invention relates to the technical field of herbicides and plant growth regulators, in particular herbicides for selective combating of broad-leaved weeds and graminaceous weeds in crops of useful plants.
It is known that phenylsulfonylureas which are substituted by heterocyclic substituents and carry an amino or a functionalized amino group on the phenyl ring have herbicidal and plant growth regulating properties (EP-A-1515; EP-A-7687 (=U.S. Pat. No. 4,383,113); EP-A-30138 (=U.S. Pat. No. 4,394,506); U.S. Pat. No. 4,892,946; U.S. Pat. No. 4,981,509; EP-A-116518 (=U.S. Pat. No. 4,664,695, U.S. Pat. No. 4,632,695)).
Phenylsulfonylureas which contain, on the phenyl ring, a carboxyl group or a function derived from the carboxyl group in the 2-position and an N-alkyl-N-acyl-amino group in the 5-position have furthermore already been proposed in German Patent Application P 42 36 902.9 (WO-94/10154).
Surprisingly, it has now been found that certain phenylsulfonyl ureas which are substituted by heterocyclic substituents are particularly suitable as herbicides and plant growth regulators.
The present invention relates to compounds of the formula (I) and salts thereof 
in which
W1 is an oxygen or sulfur atom,
W2 is an oxygen or sulfur atom,
n is 0, 1, 2 or 3, preferably 0 or 1, in particular 0,
R is halogen, alkyl or alkoxy, independently of other substituents R if n is greater than 1,
R1 is hydrogen or an unsubstituted or substituted hydrocarbon or hydrocarbonoxy radical,
R2 is hydrogen or an unsubstituted or substituted hydrocarbon radical,
or the group
NR1R2 is a heterocyclic ring having 3 to 8 ring atoms, which is unsubstituted or substituted and contains the N atom of the group NR1R2 as a hetero-ring atom and can also contain further hetero-ring atoms,
R3 is an acyl radical,
R4 is hydrogen or an aliphatic hydrocarbon radical,
X, Y independently of one another are halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, where each of the last three radicals mentioned is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy and C1-C4-alkylthio, or are C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-alkenyloxy or C3-C6-alkynyloxy, and
Z is CH or N.
In formula (I) and in the formulae used below, the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and/or substituted radicals can be in each case straight-chain or branched in the carbon skeleton. If not stated specifically, the lower carbon skeletons, for example having 1 to 4 carbon atoms or, in the case of unsaturated groups, having 2 to 4 carbon atoms, are preferred for these radicals. Alkyl radicals, including those in the composite meanings, such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, and heptyl radicals, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, and alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; and alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl which are partly or completely substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF3, CHF2, CH2F, CF3CF2, CH2FCHCl, CCl3, CHCl2 and CH2CH2Cl; haloalkoxy is, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2Cl; corresponding statements apply to haloalkenyl and other radicals substituted by halogen.
A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl, preferably alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 5 or 6 ring atoms or phenyl; corresponding statements apply to a hydrocarbonoxy radical.
Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl; aryloxy is preferably an oxy radical corresponding to the aryl radical mentioned, in particular phenoxy.
Heteroaryl or a heteroaromatic radical is a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, and also bicyclic or polycyclic aromatic or araliphatic compounds, for example quinolinyl, benzoxazolyl and the like. Heteroaryl also includes a heteroaromatic ring, which is preferably 5- or 6-membered and contains 1, 2 or 3 hetero-ring atoms, in particular from the group consisting of N, O and S. In the substituted case, the heteroaromatic ring can also be benzo-fused.
A heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it contains one or more hetero-ring atoms, preferably from the group consisting of N, O and S; it is preferably 5- or 6-membered and contains 1, 2 or 3 hetero-ring atoms. The radical can be, for example, a heteroaromatic radical or ring as defined above, or is a partly hydrogenated radical, such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl or tetrahydrofuryl. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and in addition also oxo. The oxo group can also occur on the hetero-ring atoms which can exist at various oxidation levels, for example in the case of N and S.
Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heteroaryl, a substituted bicyclic radical or ring or a substituted bicyclic radical, if appropriate with aromatic moieties, are, for example, a substituted radical which is derived from the unsubstituted parent substance, in which the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl, and the unsaturated aliphatic radicals corresponding to the saturated hydrocarbon-containing radicals mentioned, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy and the like. In the case of radicals with carbon atoms, those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Substituents from the group consisting of halogen, for example fluorine and chlorine, C1-C4-alkyl, preferably methyl or ethyl, C1-C4-haloalkyl, preferably trifluoromethyl, C1-C4-alkoxy, preferably methoxy or ethoxy, C1-C4-haloalkoxy, nitro and cyano are as a rule preferred. The substituents methyl, methoxy and chlorine are particularly preferred here.
Mono- or disubstituted amino is, for example, alkylamino, dialkylamino, acylamino, arylamino or N-aryl-N-alkylamino.
Optionally substituted phenyl is preferably phenyl which is unsubstituted or substituted once or several times, preferably up to three times by identical or different radicals from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl and o-, m- and p-methoxyphenyl.
An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid, and radicals of acids derived therefrom, such as thiocarboxylic acid or optionally N-substituted iminocarboxylic acids, or the radical of carbonic acid monoesters, optionally N-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, or phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl, such as (C1-C4-alkyl)-carbonyl, phenylcarbonyl, in which the phenyl ring can be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids.
The invention also relates to all the stereoisomers included by formula (I) and mixtures thereof. Such compounds of the formula (I) contain one or more asymmetric C atoms or also double bonds, which are not shown separately in the formula (I). The possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers and Z and E isomers, are all included by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods, or can otherwise be prepared by stereoselective reactions in combination with the use of stereochemically pure starting substances.
The compounds of the formula (I) can form salts in which the hydrogen of the xe2x80x94SO2xe2x80x94NH group or also other acidic hydrogen atoms (for example from COOH and the like) is replaced by a cation suitable for agriculture. These salts are, for example, metal salts, preferably alkali metal or alkaline earth metal salts, in particular sodium salts and potassium salts, or also ammonium salts or salts with organic amines. Salt formation can also be carried out by addition of an acid onto basic groups, such as, for example, amino and alkylamino. Suitable acids for this purpose are strong inorganic and organic acids, for example HCl, HBr, H2SO4 or HNO3. Compounds of the formula (I) according to the invention or salts thereof which are of particular interest are those in which
R1 is H or alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkynoxy, cycloalkyl, cycloalkenyl or phenyl, where each of the nine radicals mentioned last is unsubstituted or substituted and contains a total of up to 24 carbon atoms, preferably up to a total of 12, in particular up to a total of 8 carbon atoms,
R2 is H or alkyl, alkenyl or alkynyl, where each of the three radicals mentioned last is unsubstituted or substituted and contains a total of up to 24 carbon atoms, preferably up to a total of 12 carbon atoms, in particular up to a total of 8 carbon atoms,
or the group
NR1R2 is an unsubstituted or substituted heterocyclic ring of four to eight ring atoms, where the group contains up to a total of 18 carbon atoms, preferably up to a total of 12 carbon atoms,
R3 is acyl having up to 24 carbon atoms, preferably up to 12 carbon atoms, in particular up to 8 carbon atoms, and
R4 is H or alkyl, alkenyl or alkynyl, where each of the 3 radicals mentioned last contains up to 12 carbon atoms, preferably up to 5 carbon atoms.
Compounds of the formula (I) according to the invention or salts thereof which are of particular interest are those in which
R1 is H, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-alkoxy, C2-C12-alkenoxy, C2-C12-alkynoxy, C3-C8-cycloalkyl or C5-C8-cycloalkenyl, where each of the eight radicals mentioned last is unsubstituted or substituted, for example is substituted by one or more radicals from the group consisting of halogen, cyano, azido, COxe2x80x94R5, OR6, NR7R8, SR9, SOxe2x80x94R10 and SO2xe2x80x94R11, or unsubstituted or substituted phenyl,
is H, C1-C12-alkyl, C2-C12-alkenyl or C2-C12-alkynyl, where each of the three radicals mentioned last is unsubstituted or substituted, for example is substituted by one or more radicals from the group consisting of halogen, cyano, azido, COR12, OR13, NR14R15, SR16, SOxe2x80x94R17 and SO2xe2x80x94R18,
or the group
NR1R2 is a heterocyclic ring of four to eight ring atoms, which can contain up to two further hetero-ring atoms in the ring from the group consisting of N, O and S and is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C6-alkyl, NO2, N3 and CN,
R3 is COxe2x80x94R19, CSxe2x80x94R20, SO2xe2x80x94R21, SOxe2x80x94R21 or C(xe2x95x90NR21)xe2x80x94R19,
R4 is H, C1-C3-alkyl, C2-C5-alkenyl or C2-C5-alkynyl,
R5 is H, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-alkoxy, C2-C5-alkenoxy, C2-C5-alkynoxy, NR22R23 or OH,
R6 is H, C1-C5-alkyl, C1-C5-haloalkyl, C2-C5-alkenyl, C2-C5-haloalkenyl, C2-C5-alkynyl or C2-C5-haloalkynyl,
R7 is H, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-alkoxy, COxe2x80x94CH3, COxe2x80x94H or COOCH3,
R8 is H, C1-C5-alkyl, C2-C5-alkenyl or C2-C5-alkynyl or the group
NR7R8 is a heterocyclic ring of four to eight ring atoms, which can contain up to two further hetero-ring atoms in the ring from the group consisting of N, O and S and is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C6-alkyl, NO2, N3 and CN,
R9 is H, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-haloalkyl, C2-C5-haloalkenyl or C2-C5-haloalkynyl,
R10 is C1-C5-alkyl, C2-C5-alkenyl, C2 -C5-alkynyl, C1-C5-haloalkyl, C2-C5-haloalkenyl or C2-C5-haloalkynyl,
R11 is C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-haloalkyl, C2-C5-haloalkenyl, C2-C5-haloalkynyl, C1-C5-alkoxyalkyl, C3-C8-cycloalkyl or C5-C8-cycloalkenyl,
R12 is a radical analogous to R5,
R13 is a radical analogous to R6,
R14 is a radical analogous to R7,
R15 is a radical analogous to R8, or the group
NR14R15 is a group analogous to NR7R8,
R16 is a radical analogous to R9,
R17 is a radical analogous to R10,
R18 is a radical analogous to R11,
R19 is H, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-alkoxy, C1-C12-alkylthio, C2-C12-alkenoxy, C2-C12-alkynoxy, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C1-C12-alkylamino, di (C1-C6-alkyl) amino, Nxe2x80x94C1-C4-alkoxy-Nxe2x80x94C1-C4-alkylamino, where each of the 13 radicals mentioned last are unsubstituted or substituted, for example is substituted by one or more radicals from the group consisting of halogen, cyano, azido, COxe2x80x94R24, OR25, NR26R27, SR28, SOR29 and SO2R30, or an unsubstituted or substituted phenyl, phenoxy or phenylamino radical,
R20 is a radical analogous to R19,
R21 is a radical analogous to R11,
R22 is H, C1-C5-alkyl, C2-C5-alkenyl, C2 -C5-alkynyl, C1-C5-alkoxy, C2-C5-alkenoxy or C2-C5-alkynoxy, where each of the 6 radicals mentioned last is unsubstituted or substituted, for example is substituted by one or more radicals from the group consisting of halogen, cyano, azido, amino, mono- and disubstituted amino, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-alkylsulfonyl, C1-C3-alkylsulfinyl and C1-C3-alkylthio,
R23 is H, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-alkoxy or C2-C5-alkenoxy, where each of the 5 radicals mentioned last is unsubstituted or substituted, for example is substituted by one or more radicals from the group consisting of halogen, cyano, azido, amino, mono- and disubstituted amino, C1-C3-alkoxy, C1-C3-alkylthio, C1-C3-alkylsulfonyl and C1-C3-alkylsulfinyl,
or the group
NR22R23 is a heterocyclic ring analogous to NR7R8, preferably a ring of 5 or 6 ring atoms, which can contain up to 2 further hetero-ring atoms in the ring from the group consisting of N, O and S and is unsubstituted or substituted by one or more radicals from the group consisting of halogen and C1-C4-alkyl,
R24 is H, C1-C3-alkyl, C1-C3-alkoxy, NH2 or mono- or disubstituted amino,
R25 is H, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-haloalkyl, C2-C5-haloalkenyl or C2-C5-haloalkynyl,
R26 is H, C1-C3-alkyl, C1-C3-alkoxy, COxe2x80x94CH3 or COxe2x80x94H,
R27 is H, C1-C3-alkyl,
or the group
NR26R27 is a group analogous to NR22R23,
R28 is H, C1-C3-alkyl, C1-C3-haloalkyl, C2-C5-alkenyl, C2-C5-haloalkenyl, C2-C5-alkynyl or C2-C5-haloalkynyl,
R29 is C1-C5-alkyl, C1-C5-haloalkyl, C2-C5-alkenyl, C2-C5-haloalkyl, C2-C5-alkynyl or C2-C5-haloalkynyl,
R30 is analogous to R29,
W1 is O or S, preferably O,
W2 is O or S, preferably O,
X, Y independently of one another are halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio, where each of the three radicals mentioned last is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy and C1-C4-alkylthio, or are mono- or di(C1-C4-alkyl)amino, C3-C6-cycloalkyl, C3-C5-alkenyl or C3-C5-alkynyloxy, and
Z is CH or N.
Preferred compounds of the formula (I) according to the invention or salts thereof are those in which
R1 is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenoxy, C2-C6-alkynoxy or C5-C6-cycloalkyl, where each of the 7 radicals mentioned last is unsubstituted or substituted, by one or more radicals from the group consisting of halogen, cyano, azido, COxe2x80x94R5, OR6, NR7R8, SR9, SOxe2x80x94R10 and SO2xe2x80x94R11, or phenyl, which is unsubstituted or substituted by radicals from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and nitro,
R2 is H, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, where each of the three radicals mentioned last is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, azido, COR12, OR13, NR14R15, SR16, SOxe2x80x94R17 and SO2xe2x80x94R18,
or the group
NR1R2 is a heterocyclic ring of 5 or 6 ring atoms, which can contain up to two further hetero-ring atoms in the ring from the group consisting of N and O and is unsubstituted or substituted by one or more radicals from the group consisting of C1-C4-alkyl,
R3 is COxe2x80x94R19, CSxe2x80x94R20, SO2xe2x80x94R21 or C (xe2x95x90NR21)xe2x80x94R19,
R4 is H or CH3,
R5 is H, C1-C3-alkyl, C1-C3-alkoxy, NR22R23 or OH,
R6 is H, C1-C4-alkyl or C1-C4-haloalkyl,
R7 is H, C1-C3-alkyl, C1-C3-alkoxy, COxe2x80x94CH3, COxe2x80x94H or COOCH3,
R8 is H or C1-C3-alkyl,
or the group
NR7R8 is a heterocyclic ring of 5 or 6 ring atoms, which can contain up to two further hetero-ring atoms in the ring from the group consisting of N and O and is unsubstituted or substituted by one or more C1-C4-alkyl radicals,
R9 is H, C1-C3-alkyl or C1-C3-haloalkyl,
R10 is C1-C3-alkyl or C1-C3-haloalkyl,
R11 C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy-C1-C2-alkyl,
R12 is a radical analogous to R5,
R13 is a radical analogous to R6,
R14 is a radical analogous to R7,
R15 is a radical analogous to R8,
or the group
NR14R15 is a group analogous to NR7R8,
R16 is a radical analogous to R9,
R17 is a radical analogous to R10,
R18 is a radical analogous to R11,
R19 is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C2-C6-alkenoxy, C2-C6-alkynoxy, C3-C6-cycloalkyl, C1-C6-alkylamino, di-(C1-C4-alkyl)amino or Nxe2x80x94C1-C4-alkoxy-Nxe2x80x94C1-C4-alkylamino, where each of the 11 radicals mentioned last is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, COxe2x80x94R24, OR25, NR26R27, SR28, SOR29 and SO2R30, or a phenyl, phenoxy or phenylamino radical, which is unsubstituted or substituted by radicals from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and nitro,
R20 is a radical analogous to R19,
R21 is a radical analogous to R11,
R22 is H C1-C4-alkyl or C1-C4-alkoxy, where each of the 2 radicals mentioned last is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, amino, mono- and di-(C1-C4-alkyl)amino, C1-C3-alkoxy, C1-C3-alkylsulfonyl, and C1-C3-alkylthio,
R23 is H, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C5-alkoxy or C2-C5-alkenoxy, where each of the 5 radicals mentioned last is unsubstituted or substituted, for example is substituted by one or more radicals from the group consisting of halogen, cyano, azido, amino, mono- and disubstituted amino, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-alkylthio, C1-C3-alkylsulfonyl and C1-C3-alkylsulfinyl,
or the group
NR22R23 is a group analogous to NR7R8,
R24 is H, C1-C3-alkyl, C1-C3-alkoxy, NH2 or mono- or di-(C1-C4-alkyl)amino,
R25 is H, C1-C5-alkyl or C1-C5-haloalkyl,
R26 is H or C1-C3-alkyl,
R27 is H or C1-C3-alkyl,
or the group
NR26R27 is a group analogous to NR22R23,
R28 is H or C1-C3-alkyl,
R29 is C1-C5-alkyl or C1-C5-haloalkyl,
R30 is analogous to R29,
W1 is O or S, preferably O,
W2 is O or S, preferably O,
one of the radicals X and Y is halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C4-alkylthio, where each of the three radicals mentioned last is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C2-alkoxy and C1-C2-alkylthio, or mono- or di(C1-C2-alkyl)amino, preferably halogen, methyl or methoxy, and the other of the radicals X and Y is C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy or C1-C2-alkylthio, preferably methyl or methoxy, and
Z is CH or N, preferably CH.
Particularly preferred compounds of the formula (I) according to the invention or salts thereof are those in which
R1 is H, C1-C2-alkyl, C1-C2-alkoxy or phenyl, which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-haloalkyl and C1-C2-haloalkoxy,
R2 is H, C1-C2-alkyl or C1-C2-alkoxy,
or the group
NR1R2 is a heterocyclic ring of 5 or 6 ring atoms, which can contain up to one further hetero-ring atom in the ring from the group consisting of N and O and is unsubstituted or substituted by one or more C1-C2-alkyl radicals,
R3 is COxe2x80x94R19, CSxe2x80x94R20 or SO2xe2x80x94R21,
R4 is H or CH3,
R19 is H, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-alkylthio, C2-C4-alkenoxy, C2-C4-alkynoxy, C3-C6-cycloalkyl, C1-C4-alkylamino, di-(C1-C4-alkyl) amino, Nxe2x80x94C1-C2-alkoxy-Nxe2x80x94C1-C2-alkylamino, where each of the 10 radicals mentioned last is unsubstituted or substituted by one or more radicals from the group consisting of halogen and C1-C4-alkoxy, or a phenyl or phenoxy radical, which is unsubstituted or substituted by radicals from the group consisting of halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-haloalkyl and C1-C2-haloalkoxy,
R20 is a radical analogous to R19, and
R21 is C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-alkoxy-C1-C2-alkyl.
Preferred compounds of the formula (I) according to the invention are those in which the group of the formula NHR3 on the phenyl radical is in the para-position to the group CW1xe2x80x94NR1R2 and in the meta-position to the SO2 group.
Preferred compounds of the formula (I) according to the invention are also those which contain a combination of the abovementioned radicals which are preferred in each case.
The present invention furthermore relates to processes for the preparation of the compounds of the formula (I) according to the invention or of salts thereof, which comprises
a) reacting a compound of the formula (II) 
xe2x80x83with a heterocyclic carbamate of the formula (III), 
xe2x80x83in which R* is unsubstituted or substituted phenyl or C1-C4-alkyl, or
b) reacting a sulfonyl isocyanate of the formula (IV) 
xe2x80x83with a heterocyclic amine of the formula (V) 
xe2x80x83or
c) reacting a sulfonyl chloride of the formula (VI) 
xe2x80x83with a heterocyclic amine of the above formula (V) in the presence of a cyanate, for example an alkaline metal cyanate, such as sodium cyanate or potassium cyanate, or
d) reacting a sulfonamide of the above formula (II) with a (thio)isocyanate of the formula (VII) 
xe2x80x83in the presence of a suitable base, such as, for example, potassium carbonate or triethylamine,
in which, in the above formulae (II) to (VII), the radicals R, R1, R2, R3, R4, W1, W2, X, Y and Z and the index n are as defined in formula (I), and where compounds of the formula (I) in which W2 is an oxygen atom are first obtained in variants a)-c).
The sulfonamides (II), the sulfonyl isocyanates (IV) and the sulfonyl chlorides (VI) are novel compounds. The invention likewise relates to these compounds and to their preparation.
The reaction of the compounds of the formula (II) and (III) is preferably carried out under base catalysis in inert solvents, such as, for example, methylene chloride, acetonitrile, dioxane or tetrahydrofuran, at temperatures from xe2x88x9210xc2x0 C. up to the boiling point of the particular solvent. Bases which are used here are, for example, organic amine bases, such as 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU), in particular in the case where R*=(substituted) phenyl (cf. EP-A-44807), or trimethyl- or triethylaluminium, the latter in particular in the case where R*=alkyl (cf. EP-A-166 516).
The compounds of the formula (II) are obtained, for example, from N-(t-butyl)-sulfonamides of the formulae (VIII), (IX) and (X) (cf. formula VIII*, Z*=R3NHxe2x80x94) 
Starting from compounds of the formula (VIII) in which R, n, R1, R2, R3 and W1 are as defined in formula (I), compounds of the formula (II) are obtained by reaction with a strong acid. Possible strong acids are, for example, mineral acids, such as H2SO4 or HCl, or strong organic acids, such as trifluoroacetic acid. The t-butyl group is split off at temperatures of from xe2x88x9220xc2x0 C. to the particular reflux temperature of the reaction mixture, preferably at from 0xc2x0 C. to 40xc2x0 C. The reaction can be carried out in bulk or also in a solvent, such as, for example, methylene chloride or chloroform.
The compounds of the formula (VIII) are obtained, for example, from the aniline derivatives of the formula (IX) (cf. formula (VIII), R*=NH2) by reaction with suitable electrophiles, such as, for example, acid chlorides, acid anhydrides, isocyanates, thioisocyanates, sulfonyl chlorides or amidosulfonyl chlorides (in this context, cf.: A. L. J. Beckniter in J. Zabicky, xe2x80x9cThe Chemistry of Amidesxe2x80x9d, pages 73-185, Interscience, New York, 1970; E. J. Corey et al., Tetrahedron Lett. 1978, 1051; H. J. Saunders, R. J. Slocombe, Chem. Rev. 43, 203 (1948); S. Ozaki, Chem. Rev. 72, 457, 469 (1972); G. Zxc3x6lxcex2, Arzneim.-Forsch. 33, 2 (1983); Houben-Weyl-Hagemann, xe2x80x9cMethoden der organischen Chemiexe2x80x9d (Methods of organic chemistry), 4th edition, volume E4, page 485 et seq., Thieme Verlag Stuttgart, 1983; J. Golinsky, M. Mohasza, Synthesis 1978, 823; Houben-Weyl-Mxc3xcller xe2x80x9cMethoden der organischen Chemiexe2x80x9d (Methods of organic chemistry), 4th edition, volume IX, pages 338-400 and 605-622, Thieme Verlag Stuttgart, 1955; Houben-Weyl-Klarmann, xe2x80x9cMethoden der organischen Chemiexe2x80x9d (Methods of organic chemistry), 4th edition, volume E 11/2, pages 1020-22, Thieme Verlag Stuttgart, 1985; S. Krishnamurthey, Tetrahedron Lett. 23, 3315 (1982).).
The anilines (IX) mentioned are obtained by processes which are known from the literature, for example by reduction of the nitro groups from the compounds (X) (cf. formula (VIII), Z*=NO2), for example by catalytic hydrogenation or by reduction with iron in an acetic acid medium (in this context, cf.: H. Berrie, G. T. Neuhold, F. S. Spring, J. Chem. Soc. 1952, 2042; M. Freifelder, xe2x80x9cCatalytic Hydrogenation in Organic Synthesis: Procedures and Commentaryxe2x80x9d, J. Wiley and Sons, New York (1978), chapter 5).
The compounds of the formula (X) can be obtained by amidation, starting from the benzoates of the formula (XI): 
The amide formation is carried out by reacting the benzoates (XI) (Rxc2x0=alkyl) with the amines of the formula (XII). The compounds of the formula (XI) and (XII) are starting materials which are known from the literature or commercially obtainable (cf., for example, German Patent Application P 42 36 902.9), or the compounds can be prepared analogously to generally known processes.
The amides of the formulae (VIII), (IX) and (X) are novel compounds. The invention likewise relates to these compounds and to their preparation.
The following synthesis sequence, which is explained below using the example of compounds where n=0, offers an alternative access to compounds (XI) (W1=0). Starting from 2-amino-nitrobenzoic acids (XIII), for example 2-amino-4-nitrobenzoic acid (XIIIa), the corresponding benzoic acid esters (XIV) (Rxc2x0=alkyl) are obtained by conventional esterification with the corresponding alcohols (Rxc2x0OH) and a suitable acid, such as, for example, H2SO4. 
Diazotization of the amino group and subsequent reaction with SO2/CuCl2 gives the sulfonyl chloride (XV) (analogously to Meerwein, Chem. Ber. 90 (1957) 841-852). 
Ammonolysis of compounds of the formula (XV) with t-butylamine leads to the sulfonamides of the formula (XI).
The carbamates of the formula (III) required for the reaction of the compounds (II) according to variant a) are known from the literature or can be prepared analogously to known processes (cf. EP-A-70 804 or U.S. Pat. No. 4,480,101).
The phenylsulfonyl isocyanates of the formula (IV) can be prepared, for example, analogously to the processes from EP-A-184 385 from compounds of the formula (II), for example with phosgene.
The reaction of the compounds (IV) with the aminoheterocyclic compounds of the formula (V) is preferably carried out in inert, aprotic solvents, such as, for example, dioxane, acetonitrile or tetrahydrofuran, at temperatures of between 0xc2x0 C. and the boiling point of the solvent.
The reaction of the sulfonyl chlorides (VI) with the amino-heterocyclic compounds of the formula (V) and cyanates, such as sodium cyanate and potassium cyanate, is carried out, for example, in aprotic solvents, such as, for example, acetonitrile, if appropriate in the presence of bases, for example 0.5 to 2 equivalents of base, or in basic aprotic solvents, at temperatures between xe2x88x9210xc2x0 C. and 100xc2x0 C., preferably xe2x88x9210xc2x0 C. and 60xc2x0 C., in particular at from 15xc2x0 C. to 40xc2x0 C. Possible bases or basic aprotic solvents are, for example, pyridine, picoline or lutidine or a mixture of these (cf. U.S. Pat. No. 5,157,119).
The (thio)isocyanates of the formula (VII) are obtainable by processes known from the literature (EP-A-232067, EP-A-166516). The reaction of the (thio)isocyanates (VII) with compounds (II) is carried out at from xe2x88x9210xc2x0 C. to 100xc2x0 C., preferably from 20 to 100xc2x0 C., in an inert aprotic solvent, such as, for example, acetone or acetonitrile, in the presence of a suitable base, for example N(C2H5)3 or K2CO3.
The salts of the compounds of the formula (I) are preferably prepared in inert solvents, such as, for example, water, methanol, acetone, methylene chloride, tetrahydrofuran, toluene or heptane, at temperatures of from 0 to 100xc2x0 C. Suitable bases for the preparation of the salts according to the invention are, for example, alkali metal carbonates, such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, such as NaOH, KOH and Ca(OH)2, ammonia or a suitable amine base, such as triethylamine or ethanolamine. Suitable acids for the salt formation are, for example, HCl, HBr, H2SO4 or HNO3.
The xe2x80x9cinert solventsxe2x80x9d refer red to in the above process variants in each case mean solvents which are inert under the particular reaction conditions but are not required to be inert under any reaction conditions.
The compounds of the formula (I) according to the invention or salts thereof have an excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledon harmful plants. Perennial weeds which are difficult to combat and shoot from rhizomes, root stock or other permanent organs are also readily affected by the active compounds. it is irrelevant here whether the substances are applied prior to sowing, pre-emergence or post-emergence. Examples of some representatives of the mono- and dicotyledon weed flora which can be controlled by the compounds according to the invention may be mentioned specifically, without naming of these being intended as a limitation to particular species.
On the part of monocotyledon species of weeds, for example, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also persistent species of Cyperus are readily affected. In the case of dicotyledon species of weed, the action spectrum extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side and Convolvulus, Cirsium, Rumex and Artemisia among the perennial weeds.
Weeds which occur under the specific growing conditions in rice, such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are also combated outstandingly by the active compounds according to the invention.
If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely, or the weeds grow to the cotyledon stage but then stop growing, and finally die completely after three to four weeks have elapsed.
When the active compounds are applied to the green parts of plants by the post-emergence method, a drastic stop in growth likewise occurs very rapidly after the treatment, and the weed plants remain in the growth stage existing at the time of application or die completely after a certain period, so that weed competition which is harmful to crop plants is eliminated very early and lastingly in this manner.
Although the compounds according to the invention have an excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops, such as, for example, wheat, barley, rye, rice, maize, sugar beet, cotton and soya, are damaged only insignificantly or not at all. For these reasons, the present compounds are particularly suitable for selectively combating undesirable plant growth in agricultural crops of useful plants.
The substances according to the invention furthermore have outstanding growth regulatory properties in crop plants. They intervene by regulation in the endogenous plant metabolism and can therefore be used for specific influencing of plant contents and for facilitating harvesting, for example by inducing desiccation and compressed growth. They are furthermore also suitable for general control and inhibition of undesirable vegetative growth, without thereby killing the plants. Inhibition of vegetative growth plays a major role in many mono- and dicotyledon crops, since lodging can thereby be reduced or prevented completely.
The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the usual formulations. The invention therefore also relates to herbicidal and plant growth regulating compositions which comprise compounds of the formula (I) or salts thereof.
The compounds of the formula (I) or salts thereof can be formulated in various ways, depending on the biological and/or chemico-physical parameters which exist. Suitable formulation possibilities are, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), dressing compositions, granules for application by scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kxc3xcchler, xe2x80x9cChemische Technologiexe2x80x9d (Chemical Technology), volume 7, C. Hauser Verlag Munich, 4th edition, 1986, Wade van Valkenburg, xe2x80x9cPesticide Formulationsxe2x80x9d, Marcel Dekker, N.Y., 1973; K. Martens, xe2x80x9cSpray Dryingxe2x80x9d Handbook, 3rd Edition 1979, G. Goodwin Ltd. London.
The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described for example, in: Watkins, xe2x80x9cHandbook of Insecticide Dust Diluents and Carriersxe2x80x9d, 2nd Edition, Darland Books, Caldwell N.J., H.v. Olphen, xe2x80x9cIntroduction to Clay Colloid Chemistryxe2x80x9d; 2nd Edition, J. Wiley and Sons, N.Y.; C. Marsden, xe2x80x9cSolvents Guidexe2x80x9d; 2nd Edition, Interscience, N.Y. 1963; McCutcheon""s xe2x80x9cDetergents and Emulsifiers Annualxe2x80x9d, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, xe2x80x9cEncyclopedia of Surface Active Agentsxe2x80x9d, Chem. Publ. Co. Inc., N.Y. 1964; Schxc3x6nfeldt, xe2x80x9cGrenzflxc3xa4chenaktive xc3x84thylenoxidadduktexe2x80x9d (Surface-active ethylene oxide adducts), Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kxc3xcchler, xe2x80x9cChemische Technologiexe2x80x9d (Chemical Technology), volume 7, C. Hauser Verlag Munich, 4th Edition, 1986.
Combinations with other substances having a pesticidal action, such as, for example, insecticides, acaricides, other herbicides, fungicides, safeners, fertilizers and/or growth regulators, can also be prepared on the basis of these formulations, for example in the form of a finished formulation or as a tank mix.
Wettable powders are preparations which are uniformly dispersible in water and, in addition to the active compound, as well as a diluent or inert substance, also comprise surfactants of an ionic and/or nonionic nature (wetting agents, dispersing agents), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycolether-sulfates, alkane sulfonates, alkylbenzenesulfonates, the sodium salt of ligninsulfonic acid, the sodium salt of 2,2xe2x80x2-dinaphthylmethane-6,6xe2x80x2-disulfonic acid, the sodium salt of dibutylnaphthalene-sulfonate or also the sodium salt of oleoylmethyltaurine. To prepare the wettable powders, for example, the herbicidal active compounds are finely ground in customary apparatuses, such as hammer mills, blast mills and air jet mills, and mixed with the formulation auxiliaries at the same time or subsequently.
Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more surfactants of ionic and/or nonionic nature (emulsifiers). Emulsifiers which can be used are, for example: calcium salts of alkylarylsulfonic acids, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propyleneoxide/ethyleneoxide condensation products, alkylpolyethers, sorbitan esters, such as, for example, sorbitan fatty acid esters, or polyoxyethylenesorbitan esters, such as, for example, polyoxyethylenesorbitan fatty acid esters.
Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet grinding by means of commercially available bead mills and if appropriate addition of surfactants, such as have already been listed above, for example, for the other types of formulation.
Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and if appropriate surfactants, such as have already been listed above, for example, for the other types of formulation.
Granules can be fed either by spraying the active compound onto adsorbent, granular inert material or by application of active compound concentrates by means of adhesives, for example polyvinyl alcohol, the sodium salt of polyacrylic acid or mineral oils, to the surface of carriers, such as sand, kaolinites, or granular inert material. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granulesxe2x80x94if desired as a mixture with fertilizers.
Water-dispersible granules are as a rule prepared by the customary processes, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without a solid inert material.
The agrochemical formulations as a rule comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound of the formula (I) or salts thereof.
In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be, for example, 1 to 90, preferably 5 to 80% by weight. Dust-like formulations comprise 1 to 30, preferably usually 5 to 20% by weight of active compound, and sprayable solutions comprise, for example, 0.05 to 80, preferably 2 to 50% by weight of active compound. In water-dispersible granules, the active compound content depends partly on whether the active compound is in liquid or solid form and which granulating auxiliaries, fillers and the like are used. In the case of granules which are dispersible in water, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
In addition, the active compound formulations mentioned comprise, where appropriate, the particular customary adhesives, wetting agents, dispersing agents, emulsifiers, penetration agents, preservatives, antifrost agents and solvents, fillers, carriers and dyestuffs, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity.
Combination partners which can be employed for the active compounds according to the invention in mixture formulations or in a tank mix are, for example, known active compounds such as are described, for example, in Weed Research 26, 441-445 (1986), or xe2x80x9cThe Pesticide Manualxe2x80x9d, 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and literature cited therein. The following active compounds are to be mentioned, for example, as herbicides which are known from the literature and can be combined with compounds of the formula (I) (Note: The compounds are designated either with their xe2x80x9ccommon namexe2x80x9d according to the International organization for Standardization (ISO) or by their chemical name, if appropriate together with a customary code number): acetochlor; acifluorfen; aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]-oxy]-acetic acid and acetic acid methyl ester; alachlor; alloxydim; ametryn; amidosulfuron; amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazin; aziprotryn; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin; butylate; carbetamide; CDAA, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. diethyldithiocarbamic acid-2-chloroallylester; CGA 184927, i.e. 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)-oxy]-phenoxy]-propanoic acid and 2-propynyl ester; chlomethoxyfen; chloramben; chlorazifop-butyl, pirifenop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim; clomazone; clomeprop; cloproxydim; clopyralid; cyanazine; cycloate; cycloxydim; cycluron; cyperquat; cyprazine; cyprazole; 2,4-DB; dalapon; desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethazone, clomazon; dimethipin; dimetrasulfuron, cinosulfuron; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 177, i.e. 5-cyano-1(1,1-dimethylethyl)-N-methyl-3H-pyrazole-4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; F5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide; F6285, i.e. 1-[5-(N-methylsulfonyl)-amino-2,4-dichlorophenyl]-3-methyl-4-difluoromethyl-1,2,4-triazol-5-one; fenoprop; fenoxan, s. clomazon; fenoxaprop-ethyl; fenuron; flamprop-methyl; flazasulfuron; fluazifop and ester derivatives thereof; fluchloralin; flumetsulam; N-[2,6-difluorophenyl]-5-methyl-(1,2,4-triazolo-[1,5a]pyrimidine-2-sulfonamide; flumeturon; flumipropyn; fluorodifen; fluoroglycofenethyl; fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosaten; haloxyfop and ester derivatives thereof; hexazinone; Hw 52, i.e. N-(2,3-dichlorophenyl)-4-ethoxymethoxy)benzamide; imazamethabenz-methyl; imazapyr; imazaquin; imazethamethapyr; imazethapyr; imazosulfuron; ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metobromuron; metolachlor; metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT 5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenmedipham; phenisopham; phenmedipham; picloram; piperophos, piributicarb; pirifenop-butyl; pretilachlor; primisulfuronmethyl; procyazine; prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn; propachlor; propanil, propaquizafop and ester derivatives thereof; propazine, propham, propyzamide; prosulfalin, prosulfocarb; prynachlor; pyrazolinate, pyrazon; pyrazosulfuronethyl; pyrazoxyfen; pyridate; quinclorac; quinmerac; quinofop and ester derivatives thereof, quizalofop and ester derivatives thereof; quazalofop-ethyl; quizalofop-p-tefuryl; renriduron; dymron; S 275 i.e. 2-[4-chloro-2-fluoro-5-(2-propynyloxy)-phenyl]4,5,6,7-tetrahydro-2H-indazole; S 482, i.e. 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-naphthyl]-oxy]-propanoic acid and its methyl ester; sulfometuron-methyl; sulfazuron; flazasulfuron; TCA; tebutam; tebuthiuron; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6-methylphenyl)-sulfonyl]-1H-1,2,4-triazole-1-carboxamide; thiazafluron, thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin; trimeturon; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)-phenyl]-1H-tetrazole.
For use, the formulations present in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, and then applied to the plants, parts of plants, or soil on which the plants are standing or in which they are growing or are present as seed and which is used agriculturally or industrially. Dust-like formulations, soil granules and granules for scattering as well as sprayable solutions are usually not additionally diluted with further inert substances before use.
The required amount of compounds of the formula (I) to be applied varies according to the external conditions, such as temperature, humidity and nature of herbicide used, inter alia. It can vary within wide limits, for example between 0.001 and 10.0 kg/ha or more of active substance, but is preferably between 0.005 and 5 kg/ha.